Base-catalyzed cyclization of Ugi-adducts to substituted indolyl based γ-lactams

Shiri, Morteza; Mirpour‐Marzoni, Seyedeh Zeinab; Bozorgpour-Savadjani, Zahra; Soleymanifard, Bita; Kruger, Hendrik G.

doi:10.1007/s00706-014-1271-0

Cited by 20 publications

(11 citation statements)

References 22 publications

(19 reference statements)

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“…Shiri and coworkers demonstrated a base‐mediated post‐Ugi cyclization strategy to leading to biologically relevant γ‐lactams 37 (Scheme 12). [47] Ugi adduct 36 derived from 2‐formylindole, (aliphatic/aromatic) amines, 3‐chloropropanoic acid, and isocyanides underwent highly selective intramolecular cyclization to furnish a novel series of indolyl‐based γ‐butyrolactams 37 .…”

Section: Base‐mediated Post‐ugi Transformationsmentioning

confidence: 99%

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

et al. 2021

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Advances in base‐mediated post‐Ugi transformations are reported and discussed. The minireview encompasses reports showing the abstraction of an alpha proton adjacent to amide carbonyl in aldehyde‐derived Ugi adducts under basic conditions to perform intramolecular and intermolecular cyclizations. The methodologies have been broadly classified depending on the peptidyl anion trapping under metal‐free, metal‐catalyzed, microwave‐assisted, and external electrophile‐aided reaction conditions. A comprehensive analysis of the methods has been presented, highlighting the importance in synthetic and medicinal chemistry.

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Section: Base‐mediated Post‐ugi Transformationsmentioning

confidence: 99%

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

et al. 2021

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“…In a parallel investigation, the synthesis of indole-linked -lactams 80 [where Ar = 2-(1H-indole)] via a two-step Ugi-4CR followed by a K 2 CO 3 -mediated S N 2 cyclization in DMF at 100 °C was reported by Shiri and co-workers. 56 In 2012, Hulme and co-workers 57 developed a one-pot, two-step methodology for the synthesis of 1,5-disubstituted-tetrazole-linked -lactams 82 by reacting keto-ester…”

Section: Scheme 16 Syntheses Of -Lactams 69mentioning

confidence: 99%

Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions

Pharande¹

2020

Synthesis

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Lactams are very important heterocycles as a result of their presence in a wide range of bioactive molecules, natural products and drugs, and also due their utility as versatile synthetic intermediates. Due to these reasons, numerous efforts have focused on the development of effective and efficient methods for their synthesis. Compared to conventional two-component reactions, multicomponent reactions (MCRs), particularly isocyanide-based MCRs, are widely used for the synthesis of a range of small heterocycles including lactam analogues. Despite their numerous applications in almost every field of chemistry, as yet there is no dedicated review on isocyanide-based multicomponent reactions (IMCRs) concerning the synthesis of lactams. Therefore, this review presents strategies towards the synthesis of α-, β-, γ-, δ- and ε-lactams using IMCRs or IMCRs/post-transformation reactions reported in the literature between 2000 and 2020.1 Introduction2 Developments in Lactam Synthesis2.1 α-Lactams2.2 β-Lactams2.3 γ-Lactams2.3.1 General γ-Lactams2.3.2 Benzo-Fused γ-Lactams2.3.3 Spiro γ-Lactams2.3.4 α,β-Unsaturated γ-Lactams2.3.5 Polycyclic Fused γ-Lactams2.4 δ-Lactams2.5 ε-Lactams3 Conclusions

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“…Shiri et al ( 2014 ) have reported a selective synthesis for a series of novel indolyl based γ-lactams 3b by cyclization of Ugi-adducts 3a in the presence of K 2 CO 3 in DMF at 100°C within few hours (Scheme 2 ). Under the optimum conditions, adducts derived from activated anilines underwent the reaction smoothly and gave access to the corresponding lactams in moderate to good yields.…”

Section: Five-membered Heterocyclesmentioning

confidence: 99%

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

Bariwal¹,

Kaur

Voskressensky

et al. 2018

Front. Chem.

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Multicomponent reactions (MCRs) have proved as a valuable tool for organic and medicinal chemist because of their ability to introduce a large degree of chemical diversity in the product in a single step and with high atom economy. One of the dominant MCRs is the Ugi reaction, which involves the condensation of an aldehyde (or ketone), an amine, an isonitrile, and a carboxylic acid to afford an α-acylamino carboxamide adduct. The desired Ugi-adducts may be constructed by careful selection of the building blocks, opening the door for desired post-Ugi modifications. In recent times, the post-Ugi transformation has proved an important synthetic protocol to provide a variety of heterocyclic compounds with diverse biological properties. In this review, we have discussed the significant advancements reported in the recent literature with the emphasis to highlight the concepts and synthetic applications of the derived products along with critical mechanistic aspects.

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Base-catalyzed cyclization of Ugi-adducts to substituted indolyl based γ-lactams

Abstract: Post-condensation cyclization of Ugi adducts from the condensation of 2-formylindole, isocyanides, amines, and 3-chloropropanoic acid was performed selectively in the presence of K 2 CO 3 to form a series of novel substituted c-lactams.

Cited by 20 publications

References 22 publications

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

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